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    Ring Opening of Epoxides by Pendant Silanols

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    Issue Date
    2022-01-18
    Author
    Nagamalla, Someshwar
    Mague, Joel T.
    Sathyamoorthi, Shyam
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    Copyright © 2022 American Chemical Society.
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    Abstract
    We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph3C+BF4– or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic alcohols, and cis-homoallylic alcohols were all compatible and gave products from either endo- or exo-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual rearrangement to tetrahydrofuran products was observed. The utility of this methodology was demonstrated in a short preparation of protected d-arabitol.
    Description
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see doi.org/10.1021/acs.orglett.1c04310
    URI
    http://hdl.handle.net/1808/32754
    DOI
    https://doi.org/10.1021/acs.orglett.1c04310
    Collections
    • Medicinal Chemistry Scholarly Works [244]
    Citation
    Nagamalla, S., Mague, J. T., & Sathyamoorthi, S. (2022). Ring Opening of Epoxides by Pendant Silanols. Organic letters, 24(3), 939–943. https://doi.org/10.1021/acs.orglett.1c04310

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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